For hipsters, wearing Keds harks back to a simpler time; a better time when tennis shoes were appropriate anywhere, and people who dressed preppy weren't all dicks. Of course, this extremely whitewashed romanticization of history leaves out a whole bunch of terrible stuff, but who wants to remember sad things? And besides, nothing will get you through tough times/unpaid internship like a reliable pair of kicks. That and a monthly allowance from your parents.